20 wildly out-of-touch celebrity moments that left fans completely baffled

This A-lister had a full-on meltdown in the middle of the ocean during an episode of Keeping Up with the Kardashians. At the time, her diamond earrings fell out of her ears while swimming with family. She cried, telling the audience the jewelry was worth $75,000. However, her sister, Kourtney, wasn’t moved. “Kim, there’s people that are dying.” 

Kylie Jenner has undoubtedly become one of the industry’s most successful business owners with her beauty and skincare line. However, fans were rightfully annoyed with earlier reports claiming the reality star was the world’s youngest “self-made” billionaire. 

While it’s a moment that gave us a bit of second-hand embarrassment, Bella Hadid’s comparison of the average person’s childhood struggles to her not growing up with designer pieces was stunning. “I think I got my first part of Louboutins when I graduated high school,” she said. “It makes me emotional, actually, because I’m like, so happy in this picture [of me wearing them].” 

The COVID-19 pandemic was a challenge for many, including Ellen DeGeneres, who likened lockdown to being in jail. Needless to say, the disgraced talk show host faced much heat from netizens, who reminded her that living in her mansion was likely much better than she made it seem. 

During a previous interview about being a businesswoman, Kim Kardashian rattled fans by sharing a blunt message. “I have the best advice for women in business,” she said. “Get your f$%ˆing a-s up and work. It seems like nobody wants to work these days.” 

Actress Whoopi Goldberg upset social media users in September 2025 when she revealed she was unable to slow down because the world was becoming increasingly expensive. 

“Yeah, but who can afford to do that? You know, if you don’t marry well, you gotta keep working,” Goldberg said, to which the interviewer replied, “I think you can probably afford to do that by now.”

“No, not by now. Not yet,” Goldberg replied. “I gotta keep paying those bills, baby.”

During the earlier seasons of Keeping Up With the Kardashians, Kendall Jenner opened up about her desire to become a model. Years later, she was slammed by critics after implying that the show had no impact on her reaching new heights. “Of course, I had a platform, and I never took that for granted. I always knew that that was there, but that almost made my job a little bit harder. Only because people probably didn’t want to hire me because I was on a reality TV show.” 

Nothing will ever be as cringeworthy as Victoria Beckham claiming she grew up “middle class” in the Netflix docuseries The Beckhams. It didn’t take long, though, for her husband, David, to remind her that she grew up being driven around in her father’s Rolls-Royce. 

Speaking of COVID, singer Madonna also faced public backlash after sharing a message about the dangers of the disease from her seemingly expensive bathtub, which, by the way, was filled with rose petals. 

In 2020, streamer-turned-boxer Jake Paul upset some members of the public when he launched an online course, Financial Freedom Movement, designed to teach young adults how to become an internet sensation like himself. In the course, Paul told watchers to “quit your job and fire your boss” before telling his younger fans to “quit school because you’ve been lied to.” 

Kendall isn’t the only celebrity who seemingly doesn’t pay attention to money. In 2009, Mariah Carey told an interviewer that Americans get their electricity for free. No, no, Mariah—although that would be amazing. 

It wouldn’t be a list about controversial celebrity moments without Chrissy Teigen, an influencer and the wife of singer John Legend. Also, during the COVID-19 pandemic, the Lip Sync Battle host was torched by fans after boasting about the “best” restaurants to order from while “holed up at home.” Her post rubbed many the wrong way, as many small businesses were forced to cease operations due to financial challenges. 

Rapper A$AP Rocky previously revealed that he has no interest in using his music to acknowledge the struggles of marginalized people. “I’m A$AP Rocky. I didn’t sign up to be no political activist. I wanna talk about my motherf-ckin lean, my best friend dying, girls, my jiggy fashion, and inspirations in drugs.” He continued, “I can’t relate. I go back to Harlem, it’s not the same. It’s a sad story. I gotta tell you the truth. I’m in the studio, I’m in fashion houses, I’m in these b-tches drawers.” 

Taylor Swift gave the class of 2020 a special message during graduation season; however, it was overshadowed by fans who were disappointed when she shared that she missed her high school graduation because she was traveling the world while on tour. “I found myself on radio tour with my mom in rental cars, sitting on floors of airports,” she said. 

In 2013, reality star Spencer Pratt revealed that he and his wife, Heidi Montag, had “spent at least $10 million” after believing the world was going to end in 2012. “We thought, we have got to spend this money before the asteroid hits.” 

And if you ever need a reminder about how much money A-listers like the Kardashians have, Kendall once admitted she had no idea what the word “frugal” meant. “What does that mean?” she asked. “I don’t know what that means.” Oh, to have those worries. 

Dixie D’Amelio’s reasoning for not wanting to attend college? No, it wasn’t the fear of getting acclimated in a new environment. It was her worries about hearing her own music during fraternity parties. “I don’t think I could handle that level of embarrassment, being at a frat party, and someone playing my song,” she said. 

While Kendall Jenner has certainly made a name for herself in the modeling world, the reality star was slammed by fans when she revealed she didn’t take on as many jobs as her peers because she wanted to rest. “Since the beginning, we’ve been super selective about what shows I would do,” she said. “I was never one of those girls who would do like 30 shows a season or whatever the f-ck those girls do. More power to ’em. But I had a million jobs, not only catwalks but everything else.” 

In a throwback moment that’s gone viral on TikTok, Oprah had an embarrassingly out-of-touch moment when she seemingly scolded a fan who said $100 was too much for them to spend on a gift. “It’s not too expensive. It’s really not, it’s like 100-and-something dollars.” When the fan said they need a lower option, Oprah replied, “Lower than a hundred dollars?”

Kate Moss sparked global controversy years ago when she famously declared that “nothing tastes as good as skinny feels”—a statement that stands in stark contrast to today’s culture of body positivity and inclusion.